#------------------------------------------------------------------------------ #$Date: 2018-01-11 04:50:34 +0200 (Thu, 11 Jan 2018) $ #$Revision: 205058 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229942.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7229942 loop_ _publ_author_name 'Nisar, Madiha' 'Sung, Herman H-Y.' 'Puschmann, Horst' 'Lakerveld, Richard' 'Haynes, Richard' 'Williams, Ian Duncan' _publ_section_title ; 11-Azaartemisinin cocrystals with preserved lactam: acid heterosynthons ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE01875D _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety '2(C15 H23 N O4), C4 H6 O4' _chemical_formula_sum 'C34 H52 N2 O12' _chemical_formula_weight 680.77 _chemical_name_common 11-Aza:Succ _chemical_name_systematic ; ? ; _space_group_crystal_system orthorhombic _space_group_IT_number 18 _space_group_name_Hall 'P 2 2ab' _space_group_name_H-M_alt 'P 21 21 2' _symmetry_space_group_name_Hall 'P 2 2ab' _symmetry_space_group_name_H-M 'P 21 21 2' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2017-07-17 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2017-08-15 deposited with the CCDC. 2018-01-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 17.9674(7) _cell_length_b 10.3025(4) _cell_length_c 9.3723(7) _cell_measurement_reflns_used 2959 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 75.4780 _cell_measurement_theta_min 4.7070 _cell_volume 1734.90(16) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 146.00 172.00 1.00 8.00 -- 110.57 15.00 60.00 26 2 \w 5.00 58.00 1.00 3.00 -- 40.45 -99.00 60.00 53 3 \w -76.00 29.00 1.00 3.00 -- -40.45 85.00 -55.00 105 4 \w -119.00 -10.00 1.00 3.00 -- -40.45 -77.00 120.00 109 5 \w -115.00 -24.00 1.00 3.00 -- -40.45 -77.00-150.00 91 6 \w 81.00 161.00 1.00 8.00 -- 110.57 30.00 90.00 80 7 \w 62.00 144.00 1.00 8.00 -- 110.57 -77.00 -60.00 82 8 \w 58.00 129.00 1.00 8.00 -- 110.57 15.00 60.00 71 9 \w 45.00 115.00 1.00 8.00 -- 110.57-111.00-120.00 70 10 \w 36.00 139.00 1.00 8.00 -- 110.57 -30.00-120.00 103 11 \w 36.00 109.00 1.00 8.00 -- 110.57 -61.00-150.00 73 12 \w 33.00 129.00 1.00 8.00 -- 110.57 -30.00 90.00 96 13 \w 28.00 108.00 1.00 8.00 -- 110.57 -94.00 120.00 80 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0416687000 _diffrn_orient_matrix_UB_12 -0.0565001000 _diffrn_orient_matrix_UB_13 0.1293201000 _diffrn_orient_matrix_UB_21 -0.0218932000 _diffrn_orient_matrix_UB_22 -0.1198652000 _diffrn_orient_matrix_UB_23 -0.0890678000 _diffrn_orient_matrix_UB_31 0.0716154000 _diffrn_orient_matrix_UB_32 -0.0695680000 _diffrn_orient_matrix_UB_33 0.0483789000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_unetI/netI 0.0408 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 9822 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.472 _diffrn_reflns_theta_min 4.718 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90240 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 732 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.170 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details ; Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.04(14) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3114 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0455 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.5968P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1131 _refine_ls_wR_factor_ref 0.1171 _reflns_Friedel_coverage 0.726 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.991 _reflns_number_gt 2825 _reflns_number_total 3114 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block cpd5_madiha28a _cod_original_cell_volume 1734.91(16) _cod_database_code 7229942 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B) 2.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _shelx_res_file ; madiha28a.res created by SHELXL-2014/7 TITL madiha28a in P21212 #18 REM reset to P21212 #18 CELL 1.54184 17.96737 10.30255 9.37233 90 90 90 ZERR 2 0.00069 0.00038 0.00069 0 0 0 LATT -1 SYMM -X,-Y,+Z SYMM 0.5+X,0.5-Y,-Z SYMM 0.5-X,0.5+Y,-Z SFAC C H N O UNIT 68 104 4 24 L.S. 8 PLAN 20 TEMP -173 HTAB N11 O21 HTAB O22 O10 CONF BOND fmap 2 acta 133 OMIT 0 135 OMIT -3 6 10 OMIT 0 1 8 OMIT 8 0 8 OMIT 9 3 10 OMIT -2 1 9 OMIT 5 1 8 OMIT 2 1 9 OMIT -5 1 8 OMIT 2 0 10 OMIT -6 1 6 OMIT 1 1 7 OMIT 6 1 6 OMIT 1 0 9 OMIT -1 2 9 OMIT 1 2 9 OMIT -1 1 7 OMIT 19 4 5 OMIT 2 9 7 OMIT 7 2 8 OMIT 3 2 9 OMIT -1 2 11 OMIT -7 2 8 OMIT -9 3 10 OMIT 0 4 11 OMIT -1 3 7 OMIT -14 7 6 REM REM REM WGHT 0.058300 0.596800 FVAR 6.15292 O1 4 0.271504 0.505034 0.167812 11.00000 0.02106 0.01448 = 0.06014 -0.00040 -0.00160 -0.00050 O2 4 0.297151 0.640434 0.158748 11.00000 0.02569 0.01433 = 0.06227 -0.00009 0.00167 -0.00020 O3 4 0.423146 0.594273 0.165169 11.00000 0.02175 0.01886 = 0.05178 0.00283 0.00030 -0.00154 O10 4 0.332240 0.577897 0.607976 11.00000 0.03518 0.02102 = 0.05093 -0.00034 0.00157 -0.00526 N11 3 0.390141 0.546427 0.398155 11.00000 0.02390 0.01689 = 0.05141 -0.00148 -0.00001 -0.00498 H11 2 0.416521 0.606372 0.416632 11.00000 0.04334 C1 1 0.332283 0.416577 0.205346 11.00000 0.01881 0.01658 = 0.05367 -0.00139 -0.00044 0.00127 C2 1 0.400451 0.492121 0.257444 11.00000 0.02160 0.01492 = 0.05168 0.00258 -0.00194 -0.00221 AFIX 13 H2 2 0.442725 0.429229 0.263519 11.00000 -1.20000 AFIX 0 C3 1 0.363605 0.642422 0.077904 11.00000 0.02303 0.02195 = 0.05147 0.00243 0.00092 0.00441 C4 1 0.358111 0.563384 -0.058988 11.00000 0.03396 0.02699 = 0.05083 -0.00149 0.00141 -0.00032 AFIX 23 H4A 2 0.387001 0.607993 -0.134393 11.00000 -1.20000 H4B 2 0.305432 0.561434 -0.089880 11.00000 -1.20000 AFIX 0 C5 1 0.386340 0.423064 -0.046229 11.00000 0.03426 0.02695 = 0.05737 -0.01105 0.00236 -0.00147 AFIX 23 H5A 2 0.378737 0.379623 -0.139315 11.00000 -1.20000 H5B 2 0.440627 0.425836 -0.028415 11.00000 -1.20000 AFIX 0 C6 1 0.398438 0.218579 0.102864 11.00000 0.02177 0.01976 = 0.07580 -0.01153 0.00208 -0.00025 AFIX 13 H6 2 0.448789 0.249613 0.132919 11.00000 -1.20000 AFIX 0 C7 1 0.365953 0.138820 0.225220 11.00000 0.02705 0.01605 = 0.07852 -0.00499 -0.00216 -0.00095 AFIX 23 H7A 2 0.318480 0.099387 0.193660 11.00000 -1.20000 H7B 2 0.400736 0.067434 0.248752 11.00000 -1.20000 AFIX 0 C8 1 0.351865 0.219269 0.358910 11.00000 0.02648 0.01724 = 0.06911 0.00238 0.00098 -0.00142 AFIX 23 H8A 2 0.399747 0.252596 0.396190 11.00000 -1.20000 H8B 2 0.329080 0.163862 0.433343 11.00000 -1.20000 AFIX 0 C9 1 0.278733 0.417920 0.454337 11.00000 0.02645 0.01747 = 0.04925 0.00151 -0.00116 -0.00450 AFIX 13 H9 2 0.233485 0.467498 0.424510 11.00000 -1.20000 AFIX 0 C10 1 0.336490 0.518900 0.492919 11.00000 0.02453 0.01644 = 0.04780 0.00170 -0.00071 -0.00124 C11 1 0.350395 0.338755 0.069945 11.00000 0.02134 0.02097 = 0.05721 -0.00868 -0.00063 -0.00357 AFIX 13 H11A 2 0.302051 0.306478 0.030753 11.00000 -1.20000 AFIX 0 C12 1 0.300062 0.333201 0.325593 11.00000 0.02219 0.01390 = 0.05243 -0.00006 -0.00240 -0.00348 AFIX 13 H12 2 0.252747 0.294927 0.288354 11.00000 -1.20000 AFIX 0 C13 1 0.378339 0.786041 0.053118 11.00000 0.03451 0.02192 = 0.05536 0.00366 0.00242 0.00122 AFIX 137 H13A 2 0.375905 0.832416 0.144293 11.00000 -1.50000 H13B 2 0.340717 0.821062 -0.012071 11.00000 -1.50000 H13C 2 0.427889 0.797181 0.011160 11.00000 -1.50000 AFIX 0 C14 1 0.408289 0.134480 -0.030792 11.00000 0.03340 0.02751 = 0.07938 -0.01986 0.00165 -0.00059 AFIX 137 H14A 2 0.359315 0.109411 -0.067662 11.00000 -1.50000 H14B 2 0.436683 0.056361 -0.006371 11.00000 -1.50000 H14C 2 0.435165 0.183920 -0.103767 11.00000 -1.50000 AFIX 0 C15 1 0.256028 0.341762 0.587220 11.00000 0.04344 0.02372 = 0.05638 0.00439 0.00270 -0.01060 AFIX 137 H15A 2 0.218112 0.277467 0.561631 11.00000 -1.50000 H15B 2 0.235732 0.401554 0.658631 11.00000 -1.50000 H15C 2 0.299673 0.297402 0.626654 11.00000 -1.50000 AFIX 0 O21 4 0.470847 0.778541 0.488711 11.00000 0.04708 0.03451 = 0.09974 -0.02878 0.03375 -0.02012 O22 4 0.388994 0.802314 0.665915 11.00000 0.03629 0.01899 = 0.06248 -0.00354 0.01134 -0.00662 H22 2 0.374259 0.712294 0.641628 11.00000 0.08616 C21 1 0.441397 0.844455 0.580086 11.00000 0.02939 0.02376 = 0.06200 -0.00570 0.00653 -0.00505 C22 1 0.459466 0.986284 0.600443 11.00000 0.04779 0.02143 = 0.08726 -0.01354 0.02618 -0.01230 AFIX 23 H22A 2 0.435647 1.036863 0.523104 11.00000 -1.20000 H22B 2 0.437980 1.015885 0.692107 11.00000 -1.20000 AFIX 0 HKLF 4 REM madiha28a in P21212 #18 REM R1 = 0.0455 for 2825 Fo > 4sig(Fo) and 0.0519 for all 3114 data REM 228 parameters refined using 0 restraints END WGHT 0.0449 0.3938 REM Highest difference peak 0.170, deepest hole -0.205, 1-sigma level 0.041 Q1 1 0.2673 0.5171 0.0667 11.00000 0.05 0.17 Q2 1 0.2513 0.3644 0.7010 11.00000 0.05 0.17 Q3 1 0.4870 0.7687 0.5970 11.00000 0.05 0.17 Q4 1 0.2875 0.6179 0.2744 11.00000 0.05 0.16 Q5 1 0.2992 0.6569 0.0554 11.00000 0.05 0.16 Q6 1 0.3350 0.5782 0.7076 11.00000 0.05 0.16 Q7 1 0.4909 0.5564 -0.2994 11.00000 0.05 0.16 Q8 1 0.4754 0.9944 0.7141 11.00000 0.05 0.15 Q9 1 0.4011 0.7835 0.7803 11.00000 0.05 0.15 Q10 1 0.4322 0.5817 0.0536 11.00000 0.05 0.15 Q11 1 0.2741 0.5204 0.2769 11.00000 0.05 0.15 Q12 1 0.4620 0.6872 0.5567 11.00000 0.05 0.14 Q13 1 0.5000 1.0000 0.3498 10.50000 0.05 0.14 Q14 1 0.3863 0.5275 0.5034 11.00000 0.05 0.13 Q15 1 0.4170 0.5841 0.2618 11.00000 0.05 0.13 Q16 1 0.4593 0.9950 0.4907 11.00000 0.05 0.13 Q17 1 0.4731 0.7790 0.3953 11.00000 0.05 0.13 Q18 1 0.4894 0.5387 0.3857 11.00000 0.05 0.13 Q19 1 0.3878 0.8169 0.5592 11.00000 0.05 0.12 Q20 1 0.3802 0.1391 0.1057 11.00000 0.05 0.12 ; _shelx_res_checksum 61518 _olex2_date_sample_data_collection 2017-06-27 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.240 _oxdiff_exptl_absorpt_empirical_full_min 0.859 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O1 O 0.27150(12) 0.5050(2) 0.1678(3) 0.0319(6) Uani 1 1 d . O2 O 0.29715(12) 0.6404(2) 0.1587(3) 0.0341(6) Uani 1 1 d . O3 O 0.42315(12) 0.5943(2) 0.1652(3) 0.0308(6) Uani 1 1 d . O10 O 0.33224(14) 0.5779(2) 0.6080(3) 0.0357(6) Uani 1 1 d . N11 N 0.39014(16) 0.5464(3) 0.3982(4) 0.0307(7) Uani 1 1 d . H11 H 0.417(3) 0.606(4) 0.417(5) 0.043(13) Uiso 1 1 d . C1 C 0.33228(18) 0.4166(3) 0.2053(4) 0.0297(8) Uani 1 1 d . C2 C 0.40045(18) 0.4921(3) 0.2574(4) 0.0294(8) Uani 1 1 d . H2 H 0.4427 0.4292 0.2635 0.035 Uiso 1 1 calc R C3 C 0.36361(18) 0.6424(3) 0.0779(4) 0.0322(8) Uani 1 1 d . C4 C 0.3581(2) 0.5634(3) -0.0590(4) 0.0373(9) Uani 1 1 d . H4A H 0.3870 0.6080 -0.1344 0.045 Uiso 1 1 calc R H4B H 0.3054 0.5614 -0.0899 0.045 Uiso 1 1 calc R C5 C 0.3863(2) 0.4231(4) -0.0462(5) 0.0395(9) Uani 1 1 d . H5A H 0.3787 0.3796 -0.1393 0.047 Uiso 1 1 calc R H5B H 0.4406 0.4258 -0.0284 0.047 Uiso 1 1 calc R C6 C 0.39844(18) 0.2186(3) 0.1029(5) 0.0391(10) Uani 1 1 d . H6 H 0.4488 0.2496 0.1329 0.047 Uiso 1 1 calc R C7 C 0.3660(2) 0.1388(3) 0.2252(5) 0.0405(10) Uani 1 1 d . H7A H 0.3185 0.0994 0.1937 0.049 Uiso 1 1 calc R H7B H 0.4007 0.0674 0.2488 0.049 Uiso 1 1 calc R C8 C 0.35186(18) 0.2193(3) 0.3589(5) 0.0376(9) Uani 1 1 d . H8A H 0.3997 0.2526 0.3962 0.045 Uiso 1 1 calc R H8B H 0.3291 0.1639 0.4333 0.045 Uiso 1 1 calc R C9 C 0.27873(19) 0.4179(3) 0.4543(4) 0.0311(8) Uani 1 1 d . H9 H 0.2335 0.4675 0.4245 0.037 Uiso 1 1 calc R C10 C 0.33649(19) 0.5189(3) 0.4929(4) 0.0296(7) Uani 1 1 d . C11 C 0.35040(18) 0.3388(3) 0.0699(5) 0.0332(8) Uani 1 1 d . H11A H 0.3021 0.3065 0.0308 0.040 Uiso 1 1 calc R C12 C 0.30006(18) 0.3332(3) 0.3256(4) 0.0295(8) Uani 1 1 d . H12 H 0.2527 0.2949 0.2884 0.035 Uiso 1 1 calc R C13 C 0.3783(2) 0.7860(3) 0.0531(5) 0.0373(9) Uani 1 1 d . H13A H 0.3759 0.8324 0.1443 0.056 Uiso 1 1 calc GR H13B H 0.3407 0.8211 -0.0121 0.056 Uiso 1 1 calc GR H13C H 0.4279 0.7972 0.0112 0.056 Uiso 1 1 calc GR C14 C 0.4083(2) 0.1345(4) -0.0308(5) 0.0468(11) Uani 1 1 d . H14A H 0.3593 0.1094 -0.0677 0.070 Uiso 1 1 calc GR H14B H 0.4367 0.0564 -0.0064 0.070 Uiso 1 1 calc GR H14C H 0.4352 0.1839 -0.1038 0.070 Uiso 1 1 calc GR C15 C 0.2560(2) 0.3418(3) 0.5872(5) 0.0412(9) Uani 1 1 d . H15A H 0.2181 0.2775 0.5616 0.062 Uiso 1 1 calc GR H15B H 0.2357 0.4016 0.6586 0.062 Uiso 1 1 calc GR H15C H 0.2997 0.2974 0.6267 0.062 Uiso 1 1 calc GR O21 O 0.47085(17) 0.7785(3) 0.4887(4) 0.0604(10) Uani 1 1 d . O22 O 0.38899(14) 0.8023(2) 0.6659(3) 0.0393(6) Uani 1 1 d . H22 H 0.374(3) 0.712(6) 0.642(6) 0.086(19) Uiso 1 1 d . C21 C 0.4414(2) 0.8445(3) 0.5801(5) 0.0384(9) Uani 1 1 d . C22 C 0.4595(2) 0.9863(4) 0.6004(6) 0.0522(12) Uani 1 1 d . H22A H 0.4356 1.0369 0.5231 0.063 Uiso 1 1 calc R H22B H 0.4380 1.0159 0.6921 0.063 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0211(10) 0.0145(10) 0.0601(16) -0.0004(11) -0.0016(11) -0.0005(8) O2 0.0257(11) 0.0143(10) 0.0623(17) -0.0001(11) 0.0017(12) -0.0002(8) O3 0.0217(11) 0.0189(10) 0.0518(16) 0.0028(11) 0.0003(11) -0.0015(9) O10 0.0352(12) 0.0210(11) 0.0509(16) -0.0003(11) 0.0016(12) -0.0053(10) N11 0.0239(13) 0.0169(12) 0.0514(19) -0.0015(12) 0.0000(13) -0.0050(11) C1 0.0188(14) 0.0166(13) 0.054(2) -0.0014(14) -0.0004(15) 0.0013(12) C2 0.0216(15) 0.0149(14) 0.052(2) 0.0026(15) -0.0019(14) -0.0022(12) C3 0.0230(15) 0.0220(15) 0.051(2) 0.0024(16) 0.0009(16) 0.0044(13) C4 0.0340(18) 0.0270(18) 0.051(2) -0.0015(16) 0.0014(17) -0.0003(15) C5 0.0343(19) 0.0270(17) 0.057(3) -0.0111(16) 0.0024(17) -0.0015(15) C6 0.0218(16) 0.0198(16) 0.076(3) -0.0115(18) 0.0021(17) -0.0002(13) C7 0.0270(17) 0.0161(14) 0.079(3) -0.0050(17) -0.0022(18) -0.0010(13) C8 0.0265(16) 0.0172(15) 0.069(3) 0.0024(17) 0.0010(17) -0.0014(13) C9 0.0265(16) 0.0175(14) 0.049(2) 0.0015(15) -0.0012(15) -0.0045(13) C10 0.0245(15) 0.0164(14) 0.048(2) 0.0017(15) -0.0007(14) -0.0012(13) C11 0.0213(15) 0.0210(15) 0.057(2) -0.0087(16) -0.0006(15) -0.0036(13) C12 0.0222(14) 0.0139(14) 0.052(2) -0.0001(14) -0.0024(15) -0.0035(11) C13 0.0345(19) 0.0219(16) 0.055(2) 0.0037(16) 0.0024(17) 0.0012(15) C14 0.0334(19) 0.0275(18) 0.079(3) -0.0199(19) 0.002(2) -0.0006(16) C15 0.043(2) 0.0237(16) 0.056(3) 0.0044(18) 0.0027(19) -0.0106(15) O21 0.0471(16) 0.0345(15) 0.100(3) -0.0288(18) 0.0338(17) -0.0201(13) O22 0.0363(13) 0.0190(11) 0.0625(18) -0.0035(12) 0.0113(13) -0.0066(10) C21 0.0294(16) 0.0238(17) 0.062(3) -0.0057(18) 0.0065(18) -0.0051(15) C22 0.048(3) 0.0214(18) 0.087(3) -0.014(2) 0.026(2) -0.0123(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 C1 O1 O2 111.7(2) . C3 O2 O1 108.0(2) . C2 O3 C3 112.9(2) . C10 N11 C2 127.9(3) . O1 C1 C2 110.9(2) . O1 C1 C11 106.5(3) . O1 C1 C12 104.1(3) . C2 C1 C11 111.1(3) . C12 C1 C2 110.7(3) . C12 C1 C11 113.3(3) . O3 C2 N11 107.8(2) . O3 C2 C1 114.3(3) . N11 C2 C1 112.7(3) . O2 C3 O3 108.6(3) . O2 C3 C4 112.9(3) . O2 C3 C13 104.1(3) . O3 C3 C4 110.1(3) . O3 C3 C13 107.1(3) . C13 C3 C4 113.8(3) . C3 C4 C5 114.6(3) . C11 C5 C4 116.7(3) . C7 C6 C11 111.6(3) . C7 C6 C14 110.7(3) . C14 C6 C11 110.8(4) . C8 C7 C6 112.9(3) . C7 C8 C12 110.5(3) . C10 C9 C12 114.0(3) . C10 C9 C15 110.0(3) . C15 C9 C12 114.5(3) . O10 C10 N11 121.1(3) . O10 C10 C9 120.2(3) . N11 C10 C9 118.7(3) . C1 C11 C6 111.9(3) . C5 C11 C1 112.3(3) . C5 C11 C6 111.2(3) . C1 C12 C9 110.7(3) . C8 C12 C1 110.5(3) . C8 C12 C9 115.3(3) . O21 C21 O22 124.1(3) . O21 C21 C22 122.5(4) . O22 C21 C22 113.4(3) . C22 C22 C21 113.3(4) 2_675 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 O2 1.472(3) . O1 C1 1.465(4) . O2 C3 1.414(4) . O3 C2 1.422(4) . O3 C3 1.435(4) . O10 C10 1.240(4) . N11 C2 1.444(5) . N11 C10 1.341(5) . C1 C2 1.531(4) . C1 C11 1.536(5) . C1 C12 1.531(5) . C3 C4 1.523(5) . C3 C13 1.521(4) . C4 C5 1.537(5) . C5 C11 1.535(6) . C6 C7 1.527(6) . C6 C11 1.541(5) . C6 C14 1.533(6) . C7 C8 1.523(6) . C8 C12 1.530(4) . C9 C10 1.513(4) . C9 C12 1.538(5) . C9 C15 1.527(5) . O21 C21 1.214(5) . O22 C21 1.312(5) . C21 C22 1.509(5) . C22 C22 1.484(8) 2_675 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N11 H11 O21 0.80(5) 2.13(5) 2.923(4) 170(5) O22 H22 O10 0.99(6) 1.61(6) 2.585(3) 167(5) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_4 O1 O2 C3 O3 -75.5(3) . O1 O2 C3 C4 46.9(4) . O1 O2 C3 C13 170.7(3) . O1 C1 C2 O3 -50.7(4) . O1 C1 C2 N11 72.8(4) . O1 C1 C11 C5 69.1(3) . O1 C1 C11 C6 -165.1(2) . O1 C1 C12 C8 169.8(3) . O1 C1 C12 C9 -61.2(3) . O2 O1 C1 C2 12.9(4) . O2 O1 C1 C11 -108.0(3) . O2 O1 C1 C12 132.0(3) . O2 C3 C4 C5 -94.2(4) . O3 C3 C4 C5 27.3(4) . C1 O1 O2 C3 46.7(4) . C2 O3 C3 O2 36.4(4) . C2 O3 C3 C4 -87.6(3) . C2 O3 C3 C13 148.2(3) . C2 N11 C10 O10 -176.4(3) . C2 N11 C10 C9 1.0(5) . C2 C1 C11 C5 -51.8(4) . C2 C1 C11 C6 74.1(3) . C2 C1 C12 C8 -71.0(4) . C2 C1 C12 C9 58.0(3) . C3 O3 C2 N11 -101.3(3) . C3 O3 C2 C1 24.8(4) . C3 C4 C5 C11 56.0(4) . C4 C5 C11 C1 -36.2(4) . C4 C5 C11 C6 -162.4(3) . C6 C7 C8 C12 57.0(4) . C7 C6 C11 C1 49.7(4) . C7 C6 C11 C5 176.1(3) . C7 C8 C12 C1 -56.4(4) . C7 C8 C12 C9 177.2(3) . C10 N11 C2 O3 140.3(3) . C10 N11 C2 C1 13.2(4) . C10 C9 C12 C1 -44.2(4) . C10 C9 C12 C8 82.2(3) . C11 C1 C2 O3 67.5(3) . C11 C1 C2 N11 -169.0(3) . C11 C1 C12 C8 54.5(4) . C11 C1 C12 C9 -176.5(3) . C11 C6 C7 C8 -53.5(4) . C12 C1 C2 O3 -165.7(3) . C12 C1 C2 N11 -42.2(3) . C12 C1 C11 C5 -177.0(3) . C12 C1 C11 C6 -51.2(4) . C12 C9 C10 O10 -167.6(3) . C12 C9 C10 N11 15.0(4) . C13 C3 C4 C5 147.5(3) . C14 C6 C7 C8 -177.5(3) . C14 C6 C11 C1 173.6(3) . C14 C6 C11 C5 -60.0(4) . C15 C9 C10 O10 -37.4(4) . C15 C9 C10 N11 145.2(3) . C15 C9 C12 C1 -172.0(3) . C15 C9 C12 C8 -45.7(4) . O21 C21 C22 C22 -46.5(5) 2_675 O22 C21 C22 C22 136.4(3) 2_675